Senior Vacation Specialist

Company Overview

Coastal Vacation Properties is the Premier Vacation Property Management Company in Fort Myers Beach. A family-owned business, we've become successful by personalizing the needs of our clients. We offer competitive wages, bonus opportunities, and paid time off.


For over 25 years, we have managed preferred vacation rental homes of all sizes, from condos to large multi-family luxury beach homes. Our success is in prioritizing our guests' experience and working diligently to grow our vacation rental homeowners' businesses with professionalism, relationship building, and effective marketing.

Position Summary

We are seeking an experienced, motivated Senior Vacation Specialist to support our growing reservations department. This is a hybrid role combining reservation specialist responsibilities with leadership development opportunities.

The ideal candidate is highly organized, guest-focused, and experienced in vacation rental or hospitality operations. This role will begin with a primary focus on reservations and guest service, allowing the candidate to become fully familiar with our systems, portfolio, and operational procedures. As experience and familiarity with our operations grow, the position will gradually expand to include leadership responsibilities within the department.

Our team is committed to maintaining the highest level of service and professionalism, and we're looking for someone who can lead by example while supporting both guests and fellow team members.

Key Responsibilities

Reservation Specialist Duties

• Manage reservations, including payments, documentation, check-in instructions, and guest communication
• Respond to guest inquiries across all booking channels (direct, Airbnb, Vrbo, and other OTAs)
• Answer incoming phone calls and emails from guests and property owners
• Assist guests with booking questions, stay requests, and issue resolution
• Monitor and respond to guest reviews
• Coordinate with housekeeping, operations, and quality control regarding reservation updates or guest concerns
• Assist with onboarding and setup of new rental properties

Leadership & Department Oversight (assumed after training and operational familiarity)

• Train and mentor Vacation Specialist team members on systems, policies, and procedures
• Manage all HOA/Condo paperwork submittal
• Monitor team performance, productivity, and guest communication quality
• Manage department coverage
• Conduct one-on-one check-ins and assist with performance evaluations
• Provide coaching on call handling and guest service standards
• Assist with handling escalated guest concerns, refund requests, and disputes
• Review reservation correspondence to ensure accuracy and professionalism
• Maintain reservation procedures and identify opportunities to improve workflow efficiency
• Help create and maintain Standard Operating Procedures (SOPs) for reservation processes
• Monitor booking accuracy and assist in resolving issues such as double bookings or guest relocations

Reporting & Performance Monitoring

• Track weekly booking performance
• Monitor call volume, response times, and inquiry conversion
• Review guest disputes and refund requests
• Identify booking errors and ensure proper documentation and notes are maintained

Required Qualifications

• 1+ years minimum previous experience in vacation rentals, hospitality, or property management
• Experience with reservation systems ( Streamline PMS preferred )
• Strong leadership, communication, and problem-solving skills
• Highly organized with strong attention to detail
• Ability to multitask and adapt in a fast-paced environment
• Tech-savvy and comfortable learning new systems and software
• Team-oriented with a positive, professional attitude
• Ability to work Monday-Friday with occasional on-call or weekend coverage

Preferred Qualifications

• Bilingual preferred but not required

Compensation, Benefits, & Schedule

Hourly Salary

• 21-22

Benefits

• Paid time off such as PTO, sick days, and vacation days

Schedule

• Monday-Friday, On-call shifts as needed